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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Step-growth or condensation polymerization is a stepwise reaction of bi or multifunctional monomers to form long-chain polymers. As all the monomers are reactive, most of the monomers are consumed at the early stages of the reaction to form small chains of reactive oligomers, which then combine to form long polymer chains in the late stages. Hence, the reaction has to proceed for a long time to achieve high molecular weight polymers.
Many natural and synthetic polymers are produced by...
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Preparation of 1° Amines: Azide Synthesis01:22

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
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Oligomerization route to Py-Im polyamide macrocycles.

David M Chenoweth1, Daniel A Harki, Peter B Dervan

  • 1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

Organic Letters
|July 25, 2009
PubMed
Summary
This summary is machine-generated.

Researchers developed a rapid method to synthesize cyclic pyrrole-imidazole polyamides. The 8- and 16-ring DNA-binding molecules showed a preference over the 12-ring variant due to conformational differences.

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Area of Science:

  • Medicinal Chemistry
  • Molecular Biology
  • Organic Synthesis

Background:

  • Cyclic pyrrole-imidazole polyamides are sequence-specific DNA-binding small molecules.
  • These molecules are cell-permeable and can modulate gene expression.
  • Existing synthesis methods include solid-phase and solution-phase techniques.

Purpose of the Study:

  • To develop a rapid solution-phase oligomerization approach for synthesizing eight-ring symmetrical cyclic polyamides.
  • To investigate the DNA-binding properties of newly synthesized macrocycles.
  • To understand the relationship between macrocycle size and DNA binding affinity.

Main Methods:

  • Rapid solution-phase oligomerization was employed to synthesize cyclic polyamides.
  • Synthesized macrocycles included 8-, 12-, and 16-membered rings.
  • DNA binding assays were performed to evaluate the affinity of different sized macrocycles.

Main Results:

  • The synthesis yielded 8-, 12-, and 16-membered symmetrical cyclic polyamides.
  • A preference for DNA binding was observed for the 8- and 16-membered oligomers.
  • The 12-ring macrocycle exhibited reduced DNA binding affinity compared to the 8- and 16-ring systems.

Conclusions:

  • The size and conformational flexibility of cyclic polyamides influence their DNA binding specificity.
  • The developed rapid solution-phase method efficiently produces diverse macrocyclic structures.
  • These findings contribute to the design of novel small molecules for gene regulation.